On this day in 2008 Pompey’s road to FA Cup glory got under way at Portman Road with a 1-0 win against Championship Ipswich.
It was always going to be a tough ask for Jim Magilton’s side, but when the Tractor Boys’ Liam Trotter was shown a straight red for a studs-up challenge on Pedro Mendes just 24 minutes into the game, no-one saw the progressing.
Despite this, though, Ipswich continued to play well and more than matched the Blues for long periods of the game before eventually being outdone on 51 minutes by a long ball forward by Sol Campbell.
The delivery was well controlled by substitute David Nugent, who proceeded to slot past keeper Neil Alexander for what turned out to be the only goal of the game.
For Ipswich, the season would end in disappointment, missing out on the Championship play-offs by a single point.
However, for Pompey, this was just the start of a Cup run that has gone down in history.
Also on this day in 1946, Blues wing-half Jimmy Scoular made history by becoming the first player to play in the FA Cup for two different clubs in the same season.
The Scot first appeared for Gosport Borough in a preliminary round, before featuring in Pompey’s 1-0 away defeat to Birmingham in the third round.
Since then this feat has only been repeated once, by Stan Crowther, who was allowed to play for Manchester United in the 1958 competition despite having already played for Aston Villa.
In normal circumstances he would have been cup-tied but was given special dispensation in the wake of the Munich air disaster.